


How to Be a Heartbreaker

by bisexual_lucifer



Series: Brought over from Wattpad [2]
Category: Supernatural
Genre: Bad Flirting, Bisexual Dean Winchester, Castiel is Heartbroken, Dean Being an Asshole, Dean is a player, I'm Sorry, M/M, Marina and the Diamonds, Sam Winchester is Not Amused, Songfic, like really bad
Language: English
Status: Completed
Published: 2018-04-29
Updated: 2018-04-29
Packaged: 2019-04-29 18:47:35
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,965
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14478912
Author URL: https://archiveofourown.org/users/bisexual_lucifer/pseuds/bisexual_lucifer
Summary: Of course, what Dean was about to do was so injudicious in his own eyes, so unbearably wrong that he didn't know if he'd be able to face the man he loved after this. She looked so damn much like him, the thought of sleeping with her just for a false type of closure seemed almost too appealing to Dean.If only I could actually say my feelings for once, just tell him how I feel, he thought, I wouldn't be stuck where I am now, sleeping with another girl...





	How to Be a Heartbreaker

**Author's Note:**

> Hey! It's another one brought from my Wattpad (yikes..), and this time it's put to song!  
> The title and story itself is based off of 'How to Be a Heartbreaker' by Marina and the Diamonds.  
> Hope you enjoy, because I physically can't write anything but angst.

Dean sat in the run-down bar with his head in his hands, downing a shot of strong whiskey. He felt the liquid burn his throat, raising his hand to signal to the bartender, an attractive brunette (in her late 20's, it seemed). She sauntered over to Dean, leaning over the counter an excessive amount, handing him another shot of the amber liquid. _Just what I need,_ Dean thought sarcastically, _another girl to distract me from him._ He paused, glancing back at her. _Actually...._

**Rule number one, is that you gotta have fun,**

**But baby when you're done, you gotta be the first to run.**

Dean sat for a moment, his gaze going back from his whiskey to the bartender. After a bit, he flagged her down again, but not for a drink. As she walked back over, Dean put on a charming smile, one that usually swept any women (or men, for that matter) around him off their feet. She flashed back a similar smile, and he could tell she was trying her hardest to win him over. He looked up, about to speak, when he realized her eyes were a crystal blue, _almost identical to his._

He cleared his throat, "I just wanted to... introduce myself. I'm Dean, Dean Winchester." 

She stuck her hand out, and Dean immediately realized how small it was in his. 

_It feels so wrong,_ he thought, _nothing like his._

She smiled a little wider, licking her lips, "Emily Peterson, nice to... make your acquaintance, Dean," 

She paused, letting go of his hand to touch his jacket, "Nice leather jacket, makes you look... mysterious." 

Dean glanced down at her hand on his coat, then to her face. _A distraction, that's all she'll be,_ he thought, and smiled at her again, "When do you get off, Emily?" 

**Rule number two, just don't attached to, somebody you could lose.**

**So le-let me tell you,**

Emily smiled, flipping her hair over her shoulder, "In about," she checked a clock above the shelves of liquor behind the bar countertop, "a hour or so. Meet me here?"

Dean grinned at her, shrugging, "Not like I'm going anywhere, sweetheart." 

She beamed, winking at him before going over to serve another patron. Dean sighed, putting his head in his hands once again, disappointed he was having another one-night stand when he had told himself he would stop, and just confess his feelings already.

**This is how to be a heartbreaker,**

**Boys, they like a little danger.**

**We'll get him falling for a stranger, a player,**

**Singing 'I lo-lo-love you!'**

**(At least I think I do!)**

**Cause I lo-lo-lo-love you!**

Dean couldn't help but think how the girl looked so much like _him_ , but still, it had felt all wrong when she touched him. Her hands were small, soft, and pale, but _his_ were rough, calloused, tanned, much like Dean's. Her hair, a dark brown, almost black, much like _his_ , but straightened to where it ended just above her waist, whereas _his_ was short and always messy, as if he had just rolled out of bed a minute before. Her eyes, almost the exact same as his, a crystal blue like the ocean, yet _his_ held so many more emotions, telling his story, on the other hand, her eyes shone only with lust. Of course, what Dean was about to do was so injudicious in his own eyes, so unbearably wrong that he didn't know if he'd be able to face the man he loved after this. She looked so damn much like _him_ , the thought of sleeping with her just for a false type of closure seemed almost too appealing to Dean. _If only I could actually say my feelings for once, just tell him how I feel,_ he thought, _I wouldn't be stuck where I am now, sleeping with another girl..._

**Rule number three, wear your heart on your cheek,**

**But never on your sleeve, unless you wanna taste defeat.**

Meanwhile at the bunker, Sam sat at one of the tables in the library, scouring the Internet for another case he could take up with Dean. _Speaking of Dean,_ Sam thought, _where is he?_

Sam looked around to the best of his ability sitting down before standing, and walking to the kitchen. "Dean? De-" 

Sam stopped when his gaze fell to a note on the counter. _Went out to a bar. Don't wait up. Probably won't be back til morning. -D._ Sam sighed, his brother always did this. Drank his problems away, ignoring his feelings, pushing them away, pretending he was fine. Of course Sam knew that Dean has feelings towards their angel friend, he had to stand in between all the awkward conversations, the subtle gestures, the eye sex... Of course, the angel, new to human emotions, was completely oblivious to Dean's movements, his flirting shrugged off as regular talk (which ended up being a major problem on cases when he would accidentally flirt with the victim's family members), and the staring simply platonic (also a huge problem on cases). Sam sighed again, this time with more pity. If only Dean wasn't a total asshat about his emotions...

**Rule number four, gotta be looking pure,**

**Kiss him goodbye at the door, and leave him wanting more, more.**

Dean sat at the bar, having yet another shot, waiting for the bartender, Emily, to finish her shift. He had had too many shots, forgetting the exact number but knowing it was somewhere in the range to make him neglect the nefarious feeling of guilt in his gut. He knew Sam would've found the note by now, and there was no doubt in his mind that his brother was shaking his head disappointedly. Not only had Dean promised himself that he would stop with the one-night stands, he had promised Sam the same thing. A promise they both should've known he wouldn't keep. Dean knew that fate was sealed when Emily strode over to his bar stool, taking off her apron after punching herself out, ending her shift.

**This is how to be a heartbreaker,**

**Boys, they like the look of danger.**

**We'll get them falling for a stranger, a player,**

**Singing 'I lo-lo-love you!'**

**(At least I think I do!)**

**Cause I lo-lo-lo-love you!**

Her hand grabbed Dean's jacket, pulling the leather along with him out the door of the dingy bar, only turning back to wink at the green-eyed man, giggling. When she wasn't looking, Dean grimaced slightly, somewhat remembering his feelings towards his friend, his angel. 

His thoughts were cut off when they reached Baby. "Is this yours? You're quite the badass, aren't you?"

Emily smirked a little bit, climbing in the passenger seat, and he internally cringed at her poor attempt at being seductive. As he started up the Impala, and Emily eagerly spouted her address, Dean knew there was no turning back. But after too many shots of whiskey, his regret was only covered by desire.

**Girls, we do whatever it will take,**

**Cause girls don't want, we don't want our hearts to break, in two.**

**So it's better to be fake,**

**Can't risk losing in love again babe.**

As Dean drove to her house, their angel friend had heard his name at the Men of Letters bunker, and decided to drop in, thinking Sam or Dean was praying to him for help on a case. He appeared right next to Sam, who happened to be in the kitchen, reading over a note. Sam looked over at the sound of fluttering and jumped a little when he realized the angel was less than a foot away from him. He smiled a little bit in pity as the confused angel took in his surroundings, not seeing books or a laptop out for research. 

As the angel turned to glance back at him, Sam shook his head, "Dean went out," he handed the angel the note, staring as the blue eyes of his vessel read the words illegibly scrawled on it, and sighed, "Probably having another one-night stand. Damn it, I told him to stop, he promised... I'm sorry, man." 

Sam saw the defeated position that the angel had resided in, and just as he was about to get up and go get his brother, and yell at him for breaking their friend's heart, the angel held up a hand, "It's fine, Sam... He doesn't know, how could he?" 

The angel had accepted this feeling a long time ago, and as he started to learn human emotions, he realized it was called heartbreak.

**This is how to be a heartbreaker,**

**Boys, they like a little danger.**

**We'll get them falling for a stranger, a player,**

**Singing 'I lo-lo-love you!'**

Dean made his way back to the bunker, only vaguely remembering why he had ended up at the bar in the first place. All he knew was the road in front lead to the bunker, and that he had just left the house of a fairly attractive woman, who reminded him of a face he couldn't bring a name to. As he pulled up to the garage of the bunker, he parked Baby near the front of the cars, getting out before looking outside, realizing the sun was rising, and that Sam was most likely fast asleep. He crept through the bunker, making his way to his room, before he heard talking coming from the direction of the kitchen. 

Recognizing one of the voices as his brother's, Dean walked towards the kitchen until he heard a second voice, deeper than Sam's, monotone, "It's fine, Sam... he doesn't know, how could he?" 

Dean paused, standing outside the door frame, listening to his brother and his best friend, the man- well angel- he loved talk about some man that the angel seemed to love as much as Dean loved him. His shoulders slumped as he walked to his room, quietly shutting the door before laying down, putting a pillow over his head and screaming into it in frustration. _Of course he doesn't love me,_ Dean thought, rolling over as pressure built in his eyes, begging him to cry. He sniffled, _I wonder who the lucky guy is... Probably hasn't killed everyone he loves, probably isn't a screw up like me._ He drifted off to sleep, but just before he passed out, he muttered, "Goddamn it, Castiel..." 

**How to be a heartbreaker,**

**Boys, they like the look of danger.**

**We'll get them falling for a stranger, a player,**

**Singing 'I lo-lo-love you!'**

While Sam and Castiel were talking, the roar of the Impala came from the bunker's garage. Sam heard it, but took no note of it, and he could tell the angel hadn't even heard it, too caught up in what Sam was saying, too caught up in anguish. Soft footsteps stopped right outside the kitchen, but neither Sam nor Castiel heard them. They just kept talking, and it was only when Sam mentioned the time (around 6:00 in the morning, if he had heard correctly) that Castiel made a move to get up, ready to fly out, going to attend Heavenly business. 

As he stood, Castiel heard a voice, not just any voice, Dean's voice, in his head, "Goddamn it, Castiel." 

He followed the voice, surprised to see Dean asleep in his bed, trails of dried tears on his cheeks. Castiel walked up to him, smiling before remembering Dean had just embarked in another one-night stand, crushing his hope further. _I wonder who the lucky girl was.... Probably didn't mess up everything in their life like me, probably wasn't a screw up like me._ He smiled again, this time sadly, before flying out of the bunker, returning to Heaven to assist in the other angels' duties.

**Cause I lo-lo-lo-love you!**

**(At least I think I do!)**


End file.
